DL 5550 then DL 5665 at Boston
Tallahassee → Boston → Richmond
Timetable, Boston time
15:59DL 5550 from Tallahassee at the gate
15:20DL 5665 to Richmond leaves the gate
23 h 21 apart on the timetable, overnight
DL 5665 leaves 23 h 21 after DL 5550 arrives on the timetable: more than half a day, so not a connection we count.